4-isopropenyl-7,12-dimethyl-2-methylcarbonyloxy-17-oxo-(2S,4R,5R,12R,14R)-11,16,18,19-tetraoxapentacyclo[12.2.2.16,9.01,15.010,12]nonadeca-6,8-dien-5-yl acetate (Bipinnatin-F)

ID: ALA298801

PubChem CID: 44296326

Max Phase: Preclinical

Molecular Formula: C24H28O9

Molecular Weight: 460.48

Molecule Type: Small molecule

Names and Identifiers

Synonyms: Bipinnatin-F | Bipinnatin-F|CHEMBL298801

Canonical SMILES:  C=C(C)[C@H]1C[C@H](OC(C)=O)[C@@]23O[C@@H]2[C@@H](C[C@]2(C)O[C@H]2c2cc(C)c(o2)[C@@H]1OC(C)=O)OC3=O

Standard InChI:  InChI=1S/C24H28O9/c1-10(2)14-8-17(28-12(4)25)24-21(33-24)16(31-22(24)27)9-23(6)20(32-23)15-7-11(3)18(30-15)19(14)29-13(5)26/h7,14,16-17,19-21H,1,8-9H2,2-6H3/t14-,16-,17+,19-,20+,21-,23+,24-/m1/s1

Standard InChI Key:  MFRKHEQNZYVKBU-CHICZLJJSA-N

Molfile:  

     RDKit          2D

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    5.6625   -6.8917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.9875   -6.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2250   -6.6875    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    4.6167   -5.7417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.3750   -6.3750    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    6.1375   -5.4917    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.6625   -5.8292    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.1750   -7.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.7042   -5.6417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.6667   -7.2292    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    5.3625   -7.8167    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    5.9500   -4.9042    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
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    7.0750   -4.5667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2625   -8.1792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.8250   -8.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.4000   -8.5792    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
    6.7250   -4.0250    0.0000 O   0  0  0  0  0  0  0  0  0  0  0  0
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    5.5125   -6.3750    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.2875   -4.4250    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.9000   -6.6875    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    7.5917   -4.2667    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    6.3917   -8.8417    0.0000 C   0  0  0  0  0  0  0  0  0  0  0  0
    4.4531   -7.9212    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    5.3677   -6.4020    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
    6.1215   -7.7801    0.0000 H   0  0  0  0  0  0  0  0  0  0  0  0
  2  1  1  0
  3 18  1  0
  1  4  1  1
  5  3  1  0
  3  6  1  0
  7  1  1  0
  8  5  1  0
  9 12  1  0
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 11  2  1  0
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 15  9  2  0
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 12 20  1  6
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 17 22  1  1
 23 20  1  0
 24  7  2  0
 25 21  1  0
 26 25  2  0
 27 23  2  0
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  3 29  1  1
 30 15  1  0
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 32 23  1  0
 33 25  1  0
  2  4  1  0
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  5  6  1  0
 10  8  1  0
 16  8  2  0
 11 34  1  1
  5 35  1  6
  2 36  1  6
M  END

Alternative Forms

1. Parent:

   

   ALA298801

   Bipinnatin-F

Molecule Features

Natural Product: No

Oral: No

Chemical Probe: No

Parenteral: No

Molecule Type: Small molecule

Topical: No

First In Class: No

Black Box: No

Chirality: No

Availability: No

Prodrug: No

Calculated Properties

Molecular Weight: 460.48

Molecular Weight (Monoisotopic): 460.1733

AlogP: 3.00

#Rotatable Bonds: 3

Polar Surface Area: 117.10

Molecular Species: NEUTRAL

HBA: 9

HBD: ┄

#RO5 Violations: ┄

HBA (Lipinski): 9

HBD (Lipinski): ┄

#RO5 Violations (Lipinski): ┄

CX Acidic pKa: ┄

CX Basic pKa: ┄

CX LogP: 1.97

CX LogD: 1.97

Aromatic Rings: 1

Heavy Atoms: 33

QED Weighted: 0.29

Np Likeness Score: 2.93

References

1. Abramson SN, Trischman JA, Tapiolas DM, Harold EE, Fenical W, Taylor P..  (1991)  Structure/activity and molecular modeling studies of the lophotoxin family of irreversible nicotinic receptor antagonists.,  34  (6): [PMID:1676426] [10.1021/jm00110a007]

Source

Source(1):

• Scientific Literature